Chester Vacation Packages 2026 from $726

Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Country Inn & Suites by Radisson, Ashland - Hanover, VA

$726

per person

May 4 - May 10

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Richmond (RIC)

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Graduate by Hilton Richmond

Downtown Richmond

$895

per person

May 4 - May 10

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Richmond (RIC)

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a terrace are also provided.

Linden Row Inn

Downtown Richmond

$1,119

per person

May 4 - May 10

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Richmond (RIC)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. A picnic area, express check-out, and luggage storage are also on offer.

The Commonwealth

Downtown Richmond

$1,134

per person

May 4 - May 10

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Richmond (RIC)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-out, and a computer station are also on offer.

The Berkeley Hotel

Downtown Richmond

$1,075

per person

May 4 - May 10

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Richmond (RIC)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, express check-out, and a computer station are also on offer.

Top Chester hotels deals

Suburban Studios Chester

2403 W Hundred Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$74 total

Apr 20 - Apr 21

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and laundry facilities and free newspapers are also offered.

Pool

Pet friendly

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd Chester VA

Free Cancellation

$93 nightly

$108 total

Apr 5 - Apr 6

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.

Pool

Breakfast included

Fairfield Inn By Marriott Richmond Chester

12400 Redwater Creek Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$125 total

Mar 23 - Mar 24

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a gym on site, and laundry facilities and free newspapers are also offered.

Breakfast included

Pet friendly

Candlewood Suites Chester Richmond by IHG

225 E Hundred Rd Chester VA

$123 nightly

$143 total

Apr 4 - Apr 5

Total with taxes and fees

Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the self parking.

Pet friendly

Air conditioning

Hampton Inn by Hilton Chester South

12610 Chestnut Hill Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$116 total

Apr 5 - Apr 6

Total with taxes and fees

A gym, self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.

Breakfast included

Pet friendly

Omni Richmond Hotel

100 S 12th St Richmond VA

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$200 total

Apr 3 - Apr 4

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and wedding services.

Pool

Pet friendly

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Short Pump Town Center

4.5/5(467 reviews)

During your trip to Richmond, you can do some window-shopping at Short Pump Town Center. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.

Kings Dominion

4.5/5(315 reviews)

Bring the family to Kings Dominion and enjoy the excitement of this amusement park in Doswell. Experience the festivals or attend a sporting event in this family-friendly area.

G5KT01 Egyptian building historic college Richmond Virginia

Virginia Commonwealth University

4.5/5(418 reviews)

Explore the campus of Virginia Commonwealth University during your stay in Richmond. Stroll along the area's riverfront or experience its great live music.

Frequently asked questions

How much are vacation packages to Chester?

Your travel fantasies can be realized in Chester from just $726. Our affordable package deals include flights and hotels, and they'll make your booking a cinch. The only thing you'll have to focus on is getting out there and having a great time.

How long should my Chester vacation be?

An average of 2 nights is how long most people spend checking out the delights of Chester. Not sure if that'll be enough time to squeeze in everything on your to-do list? Stay another night or two so you don't miss a thing.

Where can I get the best vacation package deals for Chester?

For the perfect Chester package deal, head straight to Travelocity. Take your pick of 400 airlines and 1,000,000 properties around the world to create your dream trip — the choice is all yours!

Why should I book my Chester vacation package with Travelocity?

Nothing beats the peace of mind knowing you've bagged the best deal in town — that's our Price Match Guarantee. Add to that our impressive range of magical destinations and 24/7 team of customer service professionals and you've got the blueprint for a stress-free vacation.

Will I save money on my Chester car rental if I bundle it with hotels and flights?

With a Chester vacation package, you can combine your hotel, flight and car bookings and save a whole lot. If you want to explore the best of this impressive area, why not make a beeline for White House? This popular attraction is 110 mi from Chester. With your own rental car, you'll be there in no time.

Which airport is best for Chester?

Chester has two major airports to pick from — Richmond Intl. Airport (RIC) (12 mi away from the city center) and Newport News - Williamsburg Intl. Airport (PHF) (55 mi away from central Chester).

What is there to do in Chester?

You'll sense a certain magic in the air as you stroll the streets of Chester. Iron Bridge Sports Park and The Lazy Daisy are just two renowned sights that make this city so special, so put them at the top of your itinerary.

Where should I stay when visiting Chester?

Many travelers choose to hit the hay at the Country Inn & Suites by Radisson, Chester, VA. It's a great base for your Chester vacation.